CN1268615C - Substituted benzoylcyclohexenones - Google Patents

Abstract

The invention relates to novel substituted benzoylcyclohexenones of formula (I) in which n, A, R<1>, R<2>, R<3>, R<4>, Y and Z each have one of the meanings as cited in the description, to methods for the production thereof and to their use as herbicides.

Description

Substituted Benzoylcyclohexenones

The present invention relates to novel substituted benzoylcyclohexenones, processes for their preparation, and their use as herbicides.

Some substituted benzoylcyclohexanediones are known to have herbicidal activity (see EP-A-090 262, EP-A-135 191, EP-A-186 118, EP-A-186 119, EP-A- 186120, EP-A-319 075, WO-A-96/26200, WO-A-97/46530, WO-A-99/07688, WO-A-00/05221). However, the activity of these compounds is not satisfactory in all respects.

Therefore, the present invention provides the new substituted benzoyl cyclohexenone of formula (I)

in

n represents the number 0, 1 or 2,

A represents a single bond or an alkanediyl group (alkylene group) having 1-6 carbon atoms,

^R represents hydrogen, phenyl or alkyl having 1 to 6 carbon atoms optionally substituted by cyano, halogen, C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -alkylthio,

R ² represents hydrogen or alkyl having 1 to 6 carbon atoms optionally substituted by cyano, halogen, C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -alkylthio, or together with R ¹ represents an alkanediyl group (alkylene) having 1 to 6 carbon atoms, or together with R ¹ -when attached to the same carbon atom-and the carbon atom to which R ¹ and R ² are attached (C=O) base,

^R represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents the following groups optionally substituted by cyano, halogen or C ₁ -C ₄ -alkoxy, respectively : Alkyl, alkoxyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino or dialkylaminosulfonyl, wherein said groups have 1-6 carbon atoms,

R ⁴ represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents the following groups optionally substituted by cyano, halogen or C ₁ -C ₄ -alkoxy, respectively : Alkyl, alkoxyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino or dialkylaminosulfonyl, wherein said groups have 1-6 carbon atoms,

Y represents hydrogen, represents an alkyl group having 1 to 10 carbon atoms optionally substituted by cyano, halogen or C ₁ -C ₄ -alkoxy, represents optionally substituted by cyano, halogen, C ₁ -C ₄ Alkenyl or alkynyl, respectively having 2 to 10 carbon atoms, substituted by -alkyl-carbonyl or C ₁ -C ₄ -alkoxycarbonyl, or represents aryl or aryl, respectively, optionally substituted by Alkyl: nitro, amino, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alk Oxy-C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -halogenated alkoxy, C ₁ -C ₄ -alkylthio, C ₁ -C ₄ -halogenated alkylthio C ₁ -C ₄ -Alkylsulfinyl, C ₁ -C ₄ -Haloalkylsulfinyl, C ₁ -C ₄ -Alkylsulfonyl, C ₁ -C ₄ -Haloalkylsulfinyl, C ₁ -C ₄ -Alkyl-carbonyl, C ₁ -C ₄ -Alkoxy-carbonyl, C ₁ -C ₄ -Alkyl-carbonyl-amino, C ₁ -C ₄ -Alkoxy-carbonyl-amino, C ₁ -C ₄ -Alkyl-sulfonyl-amino, wherein the aryl or arylalkyl group has 6 or 10 carbon atoms in the aryl group, respectively, and optionally 1-4 carbon atoms in the alkyl moiety ,

and

Z represents an optionally substituted 4-membered-12-membered saturated or unsaturated monocyclic or bicyclic heterocyclic group containing 1-4 heteroatoms (up to 4 nitrogen atoms and optionally— Or or in addition (alternativ oder additiv)—an oxygen atom or a sulfur atom, or a SO group or a SO ₂ group), and the heterocyclic group also contains 1-3 oxo groups (C=O) and/ Or a thiol group (C=S) as a heterocyclic constituent unit,

- including all possible tautomeric and, if appropriate, stereoisomeric forms of the compounds of general formula (I), as well as possible salts or metal-coordinated derivatives of the compounds of general formula (I).

In the above definitions, hydrocarbon chains such as alkyl or alkanediyl are straight or branched respectively - including combinations with heteroatoms such as alkoxy.

Preferred meanings of the radicals present in the formulas above and below are indicated below.

n preferably represents the number 0 or 2.

A preferably represents a single bond or an alkanediyl group (alkylene group) having 1 to 4 carbon atoms.

R ¹ preferably represents hydrogen, phenyl or alkyl having 1 to 5 carbon atoms optionally substituted by cyano, halogen, C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -alkylthio.

R ² preferably represents hydrogen or alkyl having 1 to 5 carbon atoms optionally substituted by cyano, halogen, C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -alkylthio, or with R ¹ together represent an alkanediyl (alkylene) group having 1 to 5 carbon atoms.

^R preferably represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents alkyl optionally substituted by cyano, halogen or C ₁ -C ₄ -alkoxy, respectively , alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino or dialkylaminosulfonyl, wherein the groups have 1-5 carbon atoms.

^R preferably represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents alkyl optionally substituted by cyano, halogen or C ₁ -C ₄ -alkoxy, respectively , alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino or dialkylaminosulfonyl, wherein the groups have 1-5 carbon atoms.

Y preferably represents hydrogen, represents alkyl having 1 to 6 carbon atoms optionally substituted by cyano, halogen or C ₁ -C ₄ -alkoxy, represents optionally cyano, halogen, C ₁ -C 4 -alkoxy, respectively ₄ -Alkyl-carbonyl or C ₁ -C ₄ -alkoxycarbonyl substituted alkenyl or alkynyl, respectively, having 2 to 6 carbon atoms, or represents aryl or aryl, respectively, optionally substituted by Alkyl: nitro, amino, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, C _{1 -C 4 -alkyl, C 1 -C 4} -haloalkyl, C ₁ -C _{4 -} Alkoxy-C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -halogenated alkoxy, C ₁ -C ₄ -alkylthio, C ₁ -C ₄ -halogenated alkyl Thio, C ₁ -C ₄ -Alkylsulfinyl, C ₁ -C ₄ -Haloalkylsulfinyl, C ₁ -C ₄ -Alkylsulfonyl, C ₁ -C ₄ -Haloalkylsulfinyl, C ₁ -C ₄ -Alkyl-carbonyl, C ₁ -C ₄ -Alkoxy-carbonyl, C ₁ -C ₄ -Alkyl-carbonyl-amino, C ₁ -C ₄ -Alkoxy-carbonyl-amino, C ₁ - _C4 -Alkyl-sulfonyl-amino, wherein the aryl or arylalkyl group has 6 or 10 carbon atoms in the aryl group, respectively, and optionally 1-4 carbon atoms in the alkyl moiety atom,

Z preferably represents one of the following heterocyclyl groups:

The bonds represented by dotted lines refer to single bonds or double bonds respectively, and each heterocyclic ring preferably only carries two substituents defined by R ^and /or ^R in any combination.

Q represents oxygen or sulfur,

R ⁵ represents hydrogen, hydroxyl, mercapto, cyano, halogen, and represents optionally cyano, halogen, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkylthio, C ₁ -C ₄ - Alkylsulfinyl or C ₁ -C ₄ -alkylsulfonyl substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl, wherein The groups each have up to 6 carbon atoms in the alkyl group, represent alkylamino or dialkylamino groups, respectively optionally substituted by halogen, wherein the groups each have up to 6 carbon atoms in the alkyl group atom, representing alkenyl, alkynyl, alkenyloxy, alkenylthio, alkynylthio or alkenylamino, respectively optionally substituted by halogen, wherein said group is in alkenyl or alkynyl, respectively Having up to 6 carbon atoms, represents cycloalkyl, cycloalkoxy, cycloalkylthio, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkane, respectively optionally substituted by halogen Alkylthio or cycloalkylalkylamino, wherein said groups each have 3 to 6 carbon atoms in the cycloalkyl, and optionally up to 4 carbon atoms in the alkyl moiety, or represent Phenyl, phenoxy, phenylthio, phenylamino, benzyl, benzyloxy, benzylthio optionally substituted by halogen, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -alkoxy or benzylamino, or represent pyrrolidinyl, piperidino or morpholino, or—if two adjacent groups ^R5 and ^R5 are located on the double bond—also together with adjacent ^R5 represent benzo and R ⁶ represents hydrogen, hydroxyl, amino, alkyleneamino having up to 4 carbon atoms, alkyl, alkoxy optionally substituted by halogen or C ₁ -C ₄ -alkoxy, respectively , alkylamino, dialkylamino or alkanoylamino, wherein said group respectively has up to 6 carbon atoms in the alkyl group, or represents alkenyl, alkynyl or chain, respectively optionally substituted by halogen Alkenyloxy, wherein said radical has up to 6 carbon atoms in alkenyl or alkynyl, respectively, represents cycloalkyl, cycloalkylalkyl or cycloalkylamino, respectively optionally substituted by halogen, wherein Said groups each have 3 to 6 carbon atoms in the cycloalkyl, and optionally up to 3 carbon atoms in the alkyl moiety, or represent, respectively, optionally halogen, C ₁ -C ₄ -alkyl Or C ₁ -C ₄ -alkoxy substituted phenyl or benzyl, or together with adjacent R ⁵ or R ⁶ represent 3-5 optionally substituted by halogen or C ₁ -C ₄ -alkyl Alkanediyl of carbon atoms in which the individual substituents ^R5 and ^R6 —if two or more of them are attached to the same heterocyclic group—may have the same or different meanings within the scope of the above definitions.

n particularly preferably represents 0.

A particularly preferably represents a single bond or represents methylene, ethylene (eth-1,1-diyl) or dimethylene (eth-1,2-diyl).

^R particularly preferably represents hydrogen, phenyl or optionally cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n-propoxy, isopropoxy, methylthio, ethylthio, n-propoxy, respectively Methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or sec-butyl substituted with propylthio or isopropylthio.

^R particularly preferably represents hydrogen or represents optionally cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n-propoxy, isopropoxy, methylthio, ethylthio, n-propylthio Methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or sec-butyl substituted by radical or isopropylthio, or together with ^R represent methylene, ethylene (ethyl- 1,1-diyl), Dimethylene (Eth-1,2-diyl), Propylene (Propan-1,1-diyl) or Trimethylene (Propan-1,3-diyl) .

^R particularly preferably represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, or substituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, methoxy , ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, isopropyl Thio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio, methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, methyl Sulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, isobutylamino, sec Butylamino, tert-butylamino, dimethylamino, diethylamino, dimethylaminosulfonyl or diethylaminosulfonyl.

^R particularly preferably represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, or represents optionally cyano, fluorine, chlorine, bromine, methoxy substituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, methoxy , ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, isopropyl Thio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio, methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, methyl Sulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, isobutylamino, sec Butylamino, tert-butylamino, dimethylamino, diethylamino, dimethylaminosulfonyl or diethylaminosulfonyl.

Y particularly preferably represents hydrogen, represents methyl, ethyl, n-propyl, iso, optionally substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n-propoxy or isopropoxy Propyl, n-butyl, isobutyl, sec-butyl or tert-butyl, representing respectively optionally cyano, fluorine, chlorine, bromine, acetyl, propionyl, n-butyryl, isobutyryl, methoxy Carbonyl, ethoxycarbonyl, n-propoxycarbonyl or isopropoxycarbonyl substituted vinyl, propenyl, butenyl, pentenyl, ethynyl, propynyl or butynyl, or represent respectively optional Phenyl, naphthyl, benzyl or phenylethyl substituted by: nitro, amino, cyano, carboxy, carbamoyl, thiocarbamoyl, fluoro, chloro, bromo, iodo, methyl , ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, methoxymethyl, ethoxymethyl, methoxyethyl , ethoxyethyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, difluoromethoxy , trifluoromethoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio, difluoromethylthio , trifluoromethylthio, methylsulfinyl, ethylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, trifluoromethylsulfonyl, acetyl, propionyl, n-butyryl, isobutyryl, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, acetylamino, propionylamino, methoxycarbonylamino, ethoxycarbonylamino, Methylsulfonylamino, ethylsulfonylamino, n-propylsulfonylamino or isopropylsulfonylamino.

Z particularly preferably represents one of the following heterocyclyl groups

Q preferably represents oxygen,

R ⁵ preferably represents hydrogen, hydroxyl, mercapto, cyano, fluorine, chlorine, bromine, iodine, and represents optionally fluorine, chlorine, methoxy, ethoxy, n-propoxy, isopropoxy, n-butyl Oxygen, isobutoxy, sec-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio , tert-butylthio, methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, methylsulfonyl, ethylsulfinyl, n-propylsulfinyl or isopropyl Sulfonyl-substituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropyl Oxygen, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio , sec-butylthio, tert-butylthio, methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, methylsulfonyl, ethylsulfinyl, n-propyl Sulfonyl, isopropylsulfonyl, representing methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, isobutylamino, sec-butylamino, tert-butylamino, dimethyl ylamino, diethylamino, di-n-propylamino or diisopropylamino, representing vinyl, propenyl, butenyl, ethynyl, propynyl, butyl, optionally substituted by fluorine and/or chlorine, respectively Alkynyl, propenyloxy, butenyloxy, propenylthio, butenylthio, propenylamino or butenylamino represents cyclopropyl, cyclobutyl, Cyclopentyl, cyclohexyl, cyclopropoxy, cyclobutoxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropyl Amino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclo Pentylmethoxy, cyclohexylmethoxy, cyclopropylmethylthio, cyclobutylmethylthio, cyclopentylmethylthio, cyclohexylmethylthio, cyclopropylmethylamino, cyclobutylmethylamino, cyclo Pentylmethylamino or cyclohexylmethylamino, or represent optionally fluorine, chlorine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl phenyl, phenoxy, phenylthio, phenylamino, benzyl, benzyloxy, benzylthio or benzylamino substituted with methoxy, ethoxy, n-propoxy or isopropoxy , or—if the two adjacent groups ^R5 and ^R5 are located on a double bond—also together with adjacent ^R5 represent a benzo group. ^R preferably represents hydrogen, hydroxyl, amino, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl optionally substituted by fluorine and/or chlorine, methoxy or ethoxy, respectively radical, sec-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, methylamino, ethylamino or dimethylamino, representing vinyl optionally substituted by fluorine and/or chlorine, respectively group, propenyl, ethynyl, propynyl or propenyloxy, representing cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclo Butylmethyl, cyclopentylmethyl or cyclohexylmethyl, or represent optionally fluorine, chlorine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, methoxy, ethoxy, n-propoxy or isopropoxy substituted phenyl or benzyl, or together with adjacent R ⁵ or R ⁶ represent, respectively, optionally substituted by methyl and/or Ethyl-substituted prop-1,3-diyl (trimethylene), but-1,4-diyl (tetramethylene) or pentam-1,5-diyl (pentamethylene).

A very particularly preferably represents a single bond or represents a methylene group.

R ¹ very particularly preferably represents hydrogen, phenyl or methyl, ethyl, n-propyl or isopropyl, each optionally substituted by fluorine or chlorine.

R ² very particularly preferably represents hydrogen or methyl, ethyl, n-propyl or i-propyl, respectively optionally substituted by fluorine or chlorine, or together with R ¹ represents methylene or dimethylene.

^R very particularly preferably represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, iodine, or represents methyl, ethyl, n-propyl, respectively optionally substituted by fluorine, ammonia, methoxy or ethoxy , Isopropyl, Methoxy, Ethoxy, Methylthio, Ethylthio, Methylsulfinyl, Ethylsulfinyl, Methylsulfonyl, Ethylsulfonyl, Methylamino, Ethylamino , dimethylamino or dimethylaminosulfonyl.

^R very particularly preferably represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, iodine, or represents methyl, ethyl, n-propyl, respectively optionally substituted by fluorine, chlorine, methoxy or ethoxy , Isopropyl, Methoxy, Ethoxy, Methylthio, Ethylthio, Methylsulfinyl, Ethylsulfinyl, Methylsulfonyl, Ethylsulfonyl, Methylamino, Ethylamino , dimethylamino or dimethylaminosulfonyl.

Y very particularly preferably represents hydrogen, represents methyl, ethyl, n-propyl, Isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl for propenyl, butenyl, pentenyl, propynyl or butynyl optionally substituted by fluorine, chlorine or bromine, respectively , or represent phenyl or benzyl optionally substituted by the following groups respectively: nitro, amino, cyano, fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, Isobutyl, sec-butyl, tert-butyl, trifluoromethyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methoxy, ethoxy, n- Propoxy, isopropoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n-propylthio, isopropylthio, difluoromethylthio, trifluoromethylthio , methylsulfinyl, ethylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, trifluoromethylsulfonyl, acetyl, propionyl, methoxycarbonyl, ethyl Oxycarbonylamino, acetylamino, propionylamino, methoxycarbonylamino, ethoxycarbonylamino, methylsulfonylamino or ethylsulfonylamino.

Z very particularly preferably represents the following heterocyclyl

R ⁵ particularly preferably represents hydrogen, fluorine, chlorine, bromine, and represents optionally fluorine, chlorine, methoxy, ethoxy, n-propoxy, isopropoxy, methylthio, ethylthio, methyl Sulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl substituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, methoxy , ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butyl Thio, isobutylthio, sec-butylthio, methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, methylsulfonyl, ethylsulfinyl, n- Propylsulfonyl or isopropylsulfonyl for methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, isobutylamino, sec-butylamino, dimethylamino or Diethylamino stands for vinyl, propenyl, butenyl, ethynyl, propynyl, butynyl, propenyloxy, butenyloxy, propenylthio, respectively optionally substituted by fluorine and/or chlorine , or represent cyclopropyl, cyclopropyloxy, cyclopropylthio, cyclopropylamino, cyclopropylmethyl, cyclopropylmethoxy, cyclopropylmethyl optionally substituted by fluorine and/or chlorine, respectively Thio or cyclopropylmethylamino.

^R6 particularly preferably represents hydrogen, represents amino, represents methyl, ethyl, methoxy, ethoxy, methylamino or ethyl optionally substituted by fluorine and/or chlorine, methoxy or ethoxy, respectively Amino, representing dimethylamino, or representing cyclopropyl, cyclopropylmethyl, phenyl or benzyl optionally substituted by fluorine and/or chlorine, respectively, or together with adjacent ^R5 or ^R6 representing Propan-1,3-diyl (trimethylene), butan-1,4-diyl (tetramethylene) or pentam-1,5-diyl ( pentamethylene).

A most preferably represents methylene.

R ¹ most preferably represents hydrogen.

^R2 most preferably represents hydrogen.

^R3 most preferably represents chlorine, trifluoromethyl or methoxy.

^R4 most preferably represents chlorine, trifluoromethyl or methylsulfonyl.

Y most preferably represents hydrogen, represents methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl optionally substituted by fluorine, chlorine or methoxy, respectively, represents propenyl, butenyl, pentenyl optionally substituted by fluorine or chlorine respectively, or represents phenyl optionally substituted by the following groups: amino, cyano, fluorine, chlorine, methyl, ethyl, tri Fluoromethyl, methoxy or ethoxy.

R ⁵ very particularly preferably represents hydrogen, methyl or ethyl.

^R very particularly preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclopropyl, cyclopropylmethyl, cyclopentyl , cyclopentylmethyl, cyclohexyl, cyclohexylmethyl, phenyl or benzyl.

^R5 most preferably represents hydrogen.

R ⁶ most preferably represents methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclopropyl, cyclopropylmethyl or phenyl.

The present invention preferably also provides sodium salts, potassium salts, magnesium salts, calcium salts, ammonium salts, C ₁ -C ₄ -alkyl ammonium salts, di-(C ₁ -C ₄ -alkyl) salts of compounds of formula (I) -ammonium salts, tri-(C ₁ -C ₄ -alkyl)-ammonium salts, tetra-(C ₁ -C ₄ -alkyl)-ammonium salts, tri-(C ₁ -C ₄ -alkyl)-sulfonium salts salt, C ₅ - or C ₆ -cycloalkylammonium salt and di-(C ₁ -C ₂ -alkyl)-benzylammonium salt, wherein A, n, R ¹ , R ² , R ³ , R ⁴ , Y and Z are as defined above, or complex compounds (coordination compounds) of these compounds with metals such as copper, iron, cobalt, nickel.

According to the invention, compounds of the formula (I) which comprise combinations of the abovementioned preferred meanings are preferred.

According to the invention, compounds of the formula (I) which comprise a combination of the abovementioned particularly preferred meanings are particularly preferred.

According to the invention, compounds of the formula (I) which comprise a combination of the abovementioned very particularly preferred meanings are very particularly preferred.

According to the present invention, compounds of formula (I) comprising a combination of the abovementioned most preferred meanings are most preferred.

The general or preferred radical definitions listed above apply both to the end products of the formula (I) and correspondingly to the starting materials or intermediates required in each case for the preparation. These radical definitions are freely combined with each other, ie combinations between the stated preferred ranges are included.

The position of the radicals R ¹ , R ² , R ³ , R ⁴ and AZ can vary according to formula (I).

The radical R ³ is preferably in the (4) position of the benzene ring, particularly preferably in the (2) position.

If ^R3 is in the (2) position, the group ^R4 is preferably in the (4) position of the benzene ring.

The group AZ is preferably at the (2) position of the benzene ring, particularly preferably at the (3) position, and the substitution patterns of (2)-R ³ , (4)-R ⁴ and (3)-AZ are particularly preferred.

The present invention particularly provides compounds of the following general formulas (IA), (IB) and (IC):

In the general formulas (IA), (IB) and (IC), n, A, R ¹ , R ² , R ³ , R ⁴ , Y and Z each have the meanings given in the definitions above.

Compounds of the general formulas (IA), (IB) and (IC) in which A represents methylene are very particularly preferred.

Examples of compounds of general formula (I) according to the invention are listed in the following groups.

group 1

wherein R ³ , R ⁴ , R ⁵ and R ⁶ each have the meanings given, for example, in the table below:

R ³ (Position-)R ⁴ R ⁵ R ⁶ h - CF _{3 CH3} F - CF _{3 CH3} Cl - CF _{3 CH3} Br - CF _{3 CH3} I - CF _{3 CH3} NO ₂ - CF _{3 CH3} CN - CF _{3 CH3 CH3} - CF _{3 CH3} OCH ₃ - CF _{3 CH3} CF ₃ - CF _{3 CH3} OCHF ₂ - CF _{3 CH3} OCF ₃ - CF _{3 CH3} SO ₂ CH ₃ - CF _{3 CH3} h - OCH _{3 CH3} F - OCH _{3 CH3} Cl - OCH _{3 CH3} Br - OCH _{3 CH3} I - OCH _{3 CH3} NO ₂ - OCH _{3 CH3} CN - OCH _{3 CH3 CH3} - OCH _{3 CH3} OCH ₃ - OCH _{3 CH3} CF ₃ - OCH _{3 CH3} OCHF ₂ - OCH _{3 CH3} OCF ₃ - OCH _{3 CH3} SO ₂ CH ₃ - OCH _{3 CH3} h - SCH _{3 CH3} R ³ (Position-)R ⁴ R ⁵ R ⁶ F - SCH _{3 CH3} Cl - SCH _{3 CH3} Br - SCH _{3 CH3} I - SCH _{3 CH3} NO ₂ - SCH _{3 CH3} CN - SCH _{3 CH3 CH3} - SCH _{3 CH3} OCH ₃ - SCH _{3 CH3} CF ₃ - SCH _{3 CH3} OCHF ₂ - SCH _{3 CH3} OCF ₃ - SCH _{3 CH3} SO ₂ CH ₃ - SCH _{3 CH3} h - OC ₂ H _{5 CH3} F - OC ₂ H _{5 CH3} Cl - OC ₂ H _{5 CH3} Br - OC ₂ H _{5 CH3} I - OC ₂ H ₅ ^CH3 NO ₂ - OC ₂ H _{5 CH3} CN - OC ₂ H _{5 CH3 CH3} - OC ₂ H _{5 CH3} OCH ₃ - OC ₂ H _{5 CH3} CF ₃ - OC ₂ H _{5 CH3} OCHF ₂ - OC ₂ H _{5 CH3} OCF ₃ - OC ₂ H _{5 CH3} SO ₂ CH ₃ - OC ₂ H _{5 CH3} h - N(CH ₃ ) _{2 CH3} F - N(CH ₃ ) _{2 CH3} Cl - N(CH ₃ ) _{2 CH3}

R ³ (Position-)R ⁴ R ⁵ R ⁶ Cl - C ₂ H ₅ C ₂ H ₅ Br - C ₂ H ₅ C ₂ H ₅ CF ₃ - C ₂ H ₅ C ₂ H ₅ SO ₂ CH ₃ - C ₂ H ₅ C ₂ H ₅

group 2

wherein R ³ , R ⁴ , R ⁵ and R ⁶ each have the meanings given, for example, in Group 1 above.

group 3

wherein R ³ , R ⁴ , R ⁵ and R ⁶ each have the meanings given, for example, in Group 1 above.

group 4

wherein R ³ , R ⁴ , R ⁵ and R ⁶ each have the meanings given, for example, in Group 1 above.

Group 5

wherein R ³ , R ⁴ , R ⁵ and R ⁶ each have the meanings given, for example, in Group 1 above.

Group 6

wherein R ³ , R ⁴ , R ⁵ and R ⁶ each have the meanings given, for example, in the table below:

R ³ (Position-)R ⁴ R ⁵ R ⁶ Cl (2-)SO ² CH ³ SCH ₃ OC ₂ H ⁵ Cl (2-)SO ² CH ³ SC ₂ H ₅ OC ₂ H ₅ Cl (2-)SO ₂ CH ₃ OCH ₃ OC ₂ H ₅ Cl (2-)SO ² CH ₃ OC ₂ H ₅ OC ₂ H ₅ SO ₂ CH ₃ (2-)Cl Cl OCH ₃ SO ₂ CH ₃ (2-)Cl Br OCH ₃ SO ₂ CH ₃ (2-)Cl _CH3 OCH ₃ SO ₂ CH ₃ (2-)Cl C ₂ H ₅ OCH ₃ SO ₂ CH ₃ (2-)Cl C ₃ H ₇ OCH ₃ SO ₂ CH ₃ (2-)Cl SCH ₃ OCH ₃ SO ₂ CH ₃ (2-)Cl SC ₂ H ₅ OCH ₃ SO ₂ CH ₃ (2-)Cl OCH ₃ OC ₂ H ₅ SO ₂ CH ₃ (2-)Cl OC ₂ H ₅ OC ₂ H ⁵ SO ₂ CH ₃ (2-)Cl _CH3 OC ₂ H ₅ SO ₂ CH ₃ (2-)Cl C ₂ H ₅ OC ₂ H ₅ SO ₂ CH ₃ (2-)Cl C ₃ H ₇ OC ₂ H ₅ SO ₂ CH ₃ (2-)Cl SCH ₃ OC ₂ H ₅ SO ₂ CH ₃ (2-)Cl SC ₂ H ₅ OC ₂ H ₅ SO ₂ CH ₃ (2-)Cl OCH ₃ OC ₂ H ₅ CF ₃ (2-)Cl Br _CH3 CF ₃ (2-)Cl SCH _{3 CH3} CF ₃ (2-)Cl OCH _{3 CH3} CF ₃ (2-)Cl N(CH ₃ ) ² _CH3 CF ₃ (2-)Cl CF _{3 CH3} CF ₃ (2-)NO ² Br ^CH3 CF ₃ (2-)NO ₂ SCH _{3 CH3} CF ₃ (2-)NO ² OCH _{3 CH3} CF ₃ (2-)NO ₂ N(CH ₃ ) _{2 CH3} R ³ (Position-)R ⁴ R ⁵ R ⁶ CF ₃ (2-)NO ₂ CF _{3 CH3} CF ₃ (2-) _CH3 Br _CH3 CF ₃ (2-) _CH3 SCH _{3 CH3} CF ₃ (2-) _CH3 OCH _{3 CH3} CF ₃ (2-) _CH3 N(CH ₃ ) _{2 CH3} CF ₃ (2-) _CH3 CF _{3 CH3} CF ₃ (2-)OCH ₃ Br _CH3 CF ₃ (2-)OCH ³ SCH _{3 CH3} CF ₃ (2-)OCH ₃ OCH _{3 CH3} CF ₃ (2-)OCH ³ N(CH ₃ ) _{2 CH3} CF ₃ (2-)OCH ³ CF _{3 CH3} SO ₂ CH ₃ (2-)NO ₂ Br _CH3 SO ₂ CH ₃ (2-)NO ² SCH _{3 CH3} SO ₂ CH ₃ (2-)NO ² OCH ₃ ^CH3 SO ₂ CH ₃ (2-)NO ₂ N(CH ₃ ) _{2 CH3} SO ₂ CH ₃ (2-)NO ₂ CF _{3 CH3} SO ₂ CH ₃ (2-) CF ₃ Br _CH3 SO ₂ CH ₃ (2-) CF ³ SCH _{3 CH3} SO ₂ CH ₃ (2-) CF ₃ OCH _{3 CH3} SO ₂ CH ₃ (2-) CF ³ N(CH ₃ ) _{2 CH3} SO ₂ CH ₃ (2-) CF ₃ CF _{3 CH3} SO ₂ CH ₃ (2-)SO ₂ CH ³ Br _CH3 SO ₂ CH ₃ (2-)SO ₂ CH ₃ SCH _{3 CH3} SO ₂ CH ₃ (2-)SO ₂ CH ₃ OCH _{3 CH3} SO ₂ CH ₃ (2-)SO ² CH ₃ N(CH ₃ ) _{2 CH3} SO ₂ CH ₃ (2-)SO ₂ CH ₃ CF _{3 CH3} CN (2-)Cl Br _CH3 CN (2-)Cl SCH _{3 CH3} R ³ (Position-)R ⁴ R ⁵ R ⁶ CN (2-)Cl OCH _{3 CH3} CN (2-)Cl N(CH ₃ ) ₂ ^CH3 CN (2-)Cl CF _{3 CH3} CN (2-)NO ² Br _CH3 CN (2-)NO ₂ SCH _{3 CH3} CN (2-)NO ² OCH _{3 CH3} CN (2-)NO ₂ N(CH ³ ) _{2 CH3} CN (2-)NO ₂ CF _{3 CH3} CN (2-) CF ³ Br ^CH3 CN (2-) CF ³ SCH _{3 CH3} CN (2-) CF ³ OCH _{3 CH3} CN (2-) CF ₃ N(CH ₃ ) _{2 CH3} CN (2-) CF ₃ CF _{3 CH3} CN (2-)SO ₂ CH ₃ Br _CH3 CN (2-)SO ² CH ₃ SCH _{3 CH3} CN (2-)SO ² CH ³ OCH _{3 CH3} CN (2-)SO ₂ CH ₃ N(CH ₃ ) _{2 CH3} CN (2-)SO ² CH ₃ CF _{3 CH3} Br (2-)NO ² Br _CH3 Br (2-)NO ₂ SCH _{3 CH3} Br (2-)NO ₂ OCH _{3 CH3} Br (2-)NO ₂ N(CH ₃ ) _{2 CH3} Br (2-)NO ₂ CF _{3 CH3} Br (2-) CF ³ Br ^CH3 Br (2-) CF ₃ SCH _{3 CH3} Br (2-) CF ₃ OCH _{3 CH3} Br (2-) CF ³ N(CH ³ ) ₂ ^CH3 Br (2-) CF ₃ CF _{3 CH3}

R ³ (Position-)R ⁴ R ⁵ R ⁶ Cl (2-)OCH ₃ OCH ₃ OCH ₃ Cl (2-)OCH ₃ OC ₂ H ₅ OCH ₃ Cl (2-)OCH _{3 CH3} OC ₂ H ₅ Cl (2-)OCH ₃ C ² H ⁵ OC ₂ H ₅ Cl (2-)OCH ₃ C ₃ H ₇ OC ₂ H ₅ Cl (2-)OCH ₃ SCH ₃ OC ₂ H ₅ Cl (2-)OCH ₃ SC ₂ H ₅ OC ₂ H ₅ Cl (2-)OCH ₃ OCH ₃ OC ₂ H ₅ Cl (2-)OCH ₃ OC ₂ H ₅ OC ₂ H ₅ SO ₂ CH ₃ (2-)OCH ₃ Cl OCH ₃ SO ₂ CH ₃ (2-)OCH ₃ Br OCH ₃ SO ₂ CH ₃ (2-)OCH _{3 CH3} OCH ₃ SO ₂ CH ₃ (2-)OCH ₃ C ₂ H ₅ OCH ₃ SO ₂ CH ₃ (2-)OCH ₃ C ₃ H ₇ OCH ₃ SO ₂ CH ₃ (2-)OCH ₃ SCH ₃ OCH ₃ SO ₂ CH ₃ (2-)OCH ₃ SC ₂ H ₅ OCH ₃ SO ₂ CH ₃ (2-)OCH ₃ OCH ₃ OC ₂ H ₅ SO ₂ CH ₃ (2-)OCH ³ OC ₂ H ₅ OC ₂ H ₅ SO ₂ CH ₃ (2-)OCH ³ _CH3 OC ₂ H ₅ SO ₂ CH ₃ (2-)OCH ₃ C ₂ H ₅ OC ₂ H ₅ SO ₂ CH ₃ (2-)OCH ₃ C ₃ H ₇ OC ₂ H ₅ SO ₂ CH ₃ (2-)OCH ₃ SCH ₃ OC ₂ H ₅ SO ₂ CH ₃ (2-)OCH ₃ SC ₂ H ₅ OC ₂ H ₅ SO ₂ CH ₃ (2-)OCH ³ OCH ₃ OC ₂ H ₅ Cl (2-)F OCH _{3 CH3} Cl (2-)F OCH ₃ C ₂ H ₅ Cl (2-)F C ₂ H ₅ OCH ₃ Cl (2-)F C ₂ H ₅ C ₂ H ₅

Group 7

wherein R ³ , R ⁴ , R ⁵ and R ⁶ each have the meanings given, for example, in Group 6 above.

Group 8

wherein R ³ , R ⁴ , R ⁵ and R ⁶ each have the meanings given, for example, in Group 6 above.

Group 9

wherein R ³ , R ⁴ , R ⁵ and R ⁶ each have the meanings given, for example, in Group 6 above.

Group 10

wherein R ³ , R ⁴ , R ⁵ and R ⁶ each have the meanings given, for example, in Group 6 above.

The novel substituted benzoylcyclohexenones of formula (I) have potent and selective herbicidal activity.

The new substituted benzoyl cyclohexenone of formula (I) is obtained in this way: the cyclohexanedione substituted by formula (II)

wherein A, R ¹ , R ² , R ³ , R ⁴ and Z are as defined above,

reaction with a halogenating agent, if appropriate in the presence of reaction auxiliaries and, if appropriate, in the presence of diluents,

And—with or without intermediate separation (“reaction in situ”)—the formula (III) obtained in this way (in the first reaction step) will be obtained in a second reaction step

Halogenated cyclohexenones

wherein A, R ¹ , R ² , R ³ , R ⁴ and Z are as defined above,

X represents halogen, preferably represents fluorine or chlorine, particularly preferably represents chlorine,

Reaction with formula (IV) mercapto compound

HS-Y (IV)

in

Y as defined above,

Carrying out the reaction, if appropriate in the presence of reaction auxiliaries and, if appropriate, in the presence of diluents,

And, if appropriate, subsequently, within the definition of the substituents, the compounds of the formula (I) obtained in this way are subjected to electrophilic or nucleophilic substitution reactions or oxidation or reduction reactions according to conventional methods, or the formula ( I) Conversion of compounds into salts.

Using for example 2-[4-chloro-2-[(3,4-dimethyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-methanol Base]-benzoyl]-cyclohexane-1,3-dione and phosgene and then use thiophenol as raw material, the reaction route in the method of the present invention can be illustrated by the following reaction scheme:

Formula (II) provides a general definition of the substituted benzoylcyclohexanediones used as starting materials in the process according to the invention for the preparation of compounds of general formula (I). In the general formula (II), A, R ¹ , R ² , R ³ , R ⁴ and Z respectively preferably have the above-mentioned references to A, R ¹ , Preferred, particularly preferred, very particularly preferred or most preferred meanings for R ² , R ³ , R ⁴ and Z.

The starting materials of general formula (II) are known and/or can be prepared by processes known per se (cf. WO-A-00/05221).

The first reaction step of the process according to the invention for the preparation of compounds of general formula (I) is carried out with a halogenating agent. The halogenating agents used may be customary halogenating agents suitable for converting enols to the corresponding halogenated alkenes. Halogen preferably represents fluorine, chlorine or bromine, especially chlorine, ie preferably chlorinating or brominating agents are used. These halogenating agents preferably include phosgene, oxalyl chloride, oxalyl bromide, phosphorus (III) chloride, phosphorus (III) bromide, phosphorus oxychloride, thionyl chloride and thionyl bromide.

The first reaction step of the process according to the invention for the preparation of compounds of the general formula (I) is preferably carried out using reaction auxiliaries. Suitable reaction auxiliaries are the reaction auxiliaries customary for halogenation reactions. These reaction auxiliary agents preferably include acetonitrile, N,N-dimethylformamide, N,N-diethylformamide, N,N-dipropylformamide and N,N-dibutylformamide, and N-formamide base pyrrolidone.

Formula (IV) provides a general definition of the mercapto compounds used as starting materials in the process according to the invention for the preparation of compounds of general formula (I). In the general formula (IV), Y preferably in particular has the preferred, particularly preferred or very particularly preferred meanings already mentioned for Y above when describing the compounds of the general formula (I) according to the invention.

The starting materials of general formula (IV) are known organic chemicals for synthesis.

The second reaction step of the process according to the invention for preparing compounds of the general formula (I) is preferably carried out using reaction auxiliaries. Suitable reaction auxiliaries are generally the customary inorganic or organic bases or acid acceptors. These reaction auxiliaries preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alcoholates, such as sodium acetate, potassium acetate or calcium acetate, lithium amide, amino Sodium, Potassium Amide or Calcium Amide, Sodium, Potassium or Calcium Carbonate, Sodium, Potassium or Calcium Bicarbonate, Lithium, Sodium, Potassium or Calcium Hydroxide, Lithium Hydroxide, Sodium Hydroxide, Hydrogen Potassium oxide or calcium hydroxide, sodium methoxide, sodium ethoxide, sodium n-propoxide, sodium isopropoxide, sodium n-butoxide, sodium isobutoxide, sodium sec-butoxide or sodium tert-butoxide, potassium methoxide, potassium ethoxide, n- Potassium propoxide, potassium isopropoxide, potassium n-butoxide, potassium isobutoxide, potassium sec-butoxide or potassium tert-butoxide; also basic organic nitrogen compounds such as trimethylamine, triethylamine, tripropylamine , tributylamine, ethyldiisopropylamine, N,N-dimethylcyclohexylamine, dicyclohexylamine, ethyldicyclohexylamine, N,N-dimethylaniline, N,N- Dimethylbenzylamine, pyridine, 2-picoline, 3-picoline, 4-picoline, 2,4-lutidine, 2,6-lutidine, 3,4-bis Pyridine and 3,5-lutidine, 5-ethyl-2-picoline, 4-dimethylaminopyridine, N-methylpiperidine, 1,4-diazabicyclo[2 ,2,2]octane (DABCO), 1,5-diazabicyclo[4,3,0]non-5-ene (DBN), or 1,8-diazabicyclo[5,4 ,0] Undec-7-ene (DBU).

The first and second steps of the process according to the invention for the preparation of compounds of general formula (I) are preferably carried out using a diluent. Suitable diluents are especially inert organic solvents. These inert organic solvents include in particular aliphatic, cycloaliphatic and aromatic optionally halogenated hydrocarbons such as gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, di Chloromethane, chloroform, carbon tetrachloride; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl ether or ethylene glycol diethyl ether; ketones such as acetone, butanone or methyl isobutyl ketone; nitriles such as acetonitrile, propionitrile or butyronitrile; amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-N-formanilide , N-methylpyrrolidone or hexamethylphosphoric triamide; esters such as methyl acetate or ethyl acetate; sulfoxides such as dimethyl sulfoxide; alcohols such as methanol, ethanol, n-propanol, isopropanol, ethylene glycol Monomethyl ether or ethylene glycol monoethyl ether.

When carrying out the first and second steps of the process according to the invention, the reaction temperature can be varied within a relatively wide range. These steps are generally carried out at a temperature of -20°C to +150°C, preferably 0°C to 120°C.

The process of the invention is generally carried out in two steps at normal pressure. However, it is also possible to carry out the process according to the invention under increased or reduced pressure—generally at pressures from 0.1 bar to 10 bar.

To carry out the process according to the invention, the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one component in greater excess. The reaction is generally carried out in a suitable diluent in the presence of suitable reaction auxiliaries, and the reaction mixture is generally stirred at the desired temperature for several hours. Workup is carried out by customary methods (see Preparation Examples).

The active compounds according to the invention can be used as defoliants, desiccants, grass killers and, especially, weed killers. By weeds is understood in the broadest sense all plants that grow where they are not needed. Whether the compounds according to the invention act as total or selective herbicides depends essentially on the amount used.

The active compounds according to the invention can be used against, for example, the following plants:

Dicotyledonous weeds of the following genera: Abutilon, Amaranthus, Hogweed, Anoda, Chamomile, Aphanes, Agricarina, Daisy, Cottonia, Capsella, Felicia, Cassia , Centaurea, Chenopodium, Thistle, Convolvulaceae, Datura, Desmodium, Sorrel, Saccharomyces, Euphorbia, Mustela, Achyranthes, Sorrel Genus, Hibiscus, Ipomoea, Kochia, Night Sesame, Leptinum, Motherwort, Matricaria, Mentha, Indigo, Mullugo, Forget-me-not, Poppy, Morning Glory Genus, Plantago, Polygonum, Purslane, Ranunculus, Radish, Welding Vegetables, Spicy Leaf, Rumex, Salsola, Senecio, Esperanthus, Chrysanthemum genus, Yun Carex, Solanum, Gesneria, Apicalia, Chickweed, Dandelion, Phyllanthus, Clover, Urtica, Pomwella, Viola, Xanthium.

Dicotyledonous crops of the following genera: Arachis, Beet, Brassica, Cucumber, Squash, Helianthus, Carrot, Soybean, Cotton, Ipomoea, Lactuca, Flax, Tomato, Nicotiana, Phaseolus, Pisumum, Solanum, Vetacea.

Monocotyledonous weeds of the following genera: Goatweed, Wingweed, Bentgrass, Aperia, Apera, Avena, Brachiaria, Brome, Tribulus, Commellis, Bermudagrass, Cyperus, Astragalus, Crabgrass, Barnyardgrass, Water Chestnuts, Cricketia, Teff, Porcupine, Fescue, Prunus, Heterocarpus, White Pyramids, Coracis, Echinacea, Heliconia, Pleurophyllum, Panicum, Paspalum, Azalea, Timothy, Bluegrass, Cymbidium, Arthrophyllum, Plant Grass, Setaria, and Sorghum.

Monocotyledonous crops of the following genera: Allium, Pineapple, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Rye, Sorghum, Triticale, Triticum, Zea .

However, the use of the active compounds according to the invention is by no means restricted to plants of these genera, but can also be extended to other plants in the same manner.

Depending on the concentration, the active compounds according to the invention are suitable for controlling all weeds on, for example, industrial grounds and railway tracks, as well as roads and yards with and without tree growth. Likewise, the active compounds according to the invention can be used for controlling perennial crops such as forests, ornamental forests, orchards, vineyards, citrus orchards, nut orchards, banana groves, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations for weed control in orchards, berry plantations and hop fields, and for the control of weeds in lawns, meadows and pastures, and for the selective control of weeds in annual crops.

When used in soil and above-mentioned plant cultivation land, the compound of the formula (I) of the present invention has strong herbicidal activity and broad activity spectrum. To a certain extent, they are also suitable for the selective control of monocotyledonous and dicotyledonous weeds in both monocotyledonous and dicotyledonous crops by pre- and post-emergence methods.

At certain concentrations or application rates, the active compounds according to the invention can also be used for controlling animal pests and fungal or bacterial plant diseases. If appropriate, they can also be used as intermediates or precursors for the synthesis of other active compounds.

According to the invention, all plants and plant parts can be treated. In this context, plants are understood to include all plants and plant populations, such as desired and undesired wild plants or crops (including native crops). Crops may be plants obtainable by conventional breeding and optimization methods, or by biotechnological and genetic engineering methods or a combination of these methods, including transgenic plants, and including plant varieties which may or may not be protected by plant variety rights. Plant parts are understood to mean all above-ground and underground parts and organs of plants, such as buds, leaves, flowers and roots, examples which may be mentioned are leaves, needles, stems, trunks, flowers, buds, fruits and seeds and roots, tubers and rhizomes. Plant parts also include harvested plants and vegetative and reproductive propagating material, such as seedlings, tubers, rhizomes, cuttings and seeds.

The treatment of plants and plant parts with the active compounds according to the invention can be carried out directly or by allowing the compounds to act on their environment, habitat or storage area according to customary treatment methods, for example by soaking, spraying, evaporating, atomizing, sprinkling, brushing Coatings are used to apply the active compounds, and to propagation material, in particular to seeds, by application of a single or multiple coatings.

The active compounds according to the invention can be converted into customary preparations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, suspensions-emulsion concentrates, impregnated with active compounds Natural or synthetic substances, and microcapsules in polymers.

These formulations can be prepared by known methods, for example by mixing the active compounds with extenders, i.e. liquid solvents and/or solid carriers, and optionally using surfactants, i.e. emulsifiers and/or dispersants and/or foam forming agents agent to make.

If the compatibilizer used is water, it is also possible, for example, to use organic solvents as auxiliary solvents. Suitable liquid solvents are mainly: aromatic solvents such as xylene, toluene or alkylnaphthalene, chlorinated aromatic and chlorinated aliphatic hydrocarbons such as chlorobenzene, vinyl chloride or methylene chloride, aliphatic hydrocarbons such as cyclohexane or Paraffins such as petroleum distillates, mineral and vegetable oils, alcohols such as butanol or diols, and ethers and esters thereof, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethylsulfoxide, and water.

Suitable solid carriers are: for example ammonium salts and natural mineral powders such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and synthetic mineral powders such as highly disperse silicon dioxide, Alumina and silicates; suitable solid carriers for granules are, for example, crushed or graded natural rocks, such as calcite, marble, pumice, sepiolite, dolomite, and synthetic inorganic and organic powders and organic materials such as Sawdust, coconut shells, pieces of corn cobs, particles of tobacco stalks; suitable emulsifiers and/or foam formers are, for example, nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers For example, alkyl aryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolysates; suitable dispersants are: for example lignosulfite waste liquor and methyl cellulose .

Viscosifiers such as carboxymethylcellulose, natural and synthetic polymers such as gum arabic, polyvinyl alcohol and polyvinyl acetate in the form of powders, granules or latexes, and natural phospholipids such as cephalins and lecithins can be used in the formulations, with synthetic phospholipids. Other additives may be mineral and vegetable oils.

Colorants such as inorganic pigments such as iron oxide, titanium oxide, Prussian blue, and organic dyes such as alizarin dyes, azo dyes and metal phthalocyanines, and micronutrients such as iron, manganese, boron, copper, cobalt, Salts of molybdenum and zinc.

The formulations generally contain 0.1-95% by weight of active compound, preferably 0.5-90% by weight of active compound.

For the control of weeds, the active compounds according to the invention, in their own form or in their formulations, can also be used as mixtures with known herbicides and/or substances which improve crop compatibility ("safeners"), finished formulations or Canned mixes are all available. Mixtures with herbicides comprising one or more known herbicides and safeners are therefore also feasible.

Possible components of the mixture are known herbicides, such as: Acetochlor, Acifluorfen, Acifluben, Alachlor, Mofen, Ametim, Amicarbazone, Amidochlor, Amidosulfuron , sampophos, sulfazone, atrazine, Azafenidin, rimsulfuron-methyl, Beflubutamid, azafen, furazone, bensulfuron-methyl, bentazone, Benzfendizone, Benzobicyclon, methazolone, Xinyan Ling, bialafosine, fluoride, bispyribac, bromobutyramide, bromophenoxim, bromoxynil, butachlor, Butafenacil(-allyl), Butroxydim, sudalim, benzoconazole, Caloxydim, Bisamid, Carfentrazone(-ethyl), Methoxypyr, Fabacetin, Chlorachlor, Chlorsulfuron-methyl, Cyclofen, Chlorsulfuron, Chlorotocuron, Cinidon(-ethyl), Cycloheptazol Ether, etesulfuron, Clefoxydim, clethodim, clodinafop, clomazone, chloroformamide, clopyralid, Clopyrasulfuron(-methyl), Cloransulam(-methyl), Cumyluron, cyanoacethydrazide, Cybutryne . Diclopyr, Diclosulam, Metolachlor, Phyllostachys, Diflufenazole, Diflufenzopyr, Zuron, Diclosulam, Metolachlor, Isoamyl, Dimethenamid, Dimexyflam, Dimethonine , Grass Naidel, Diquat, Dithiopyr, Diuron, Dymron, Epropodan, EPTC, Pentrapyr, Ethoxyfen, Ethoxysulfuron, Etobenzanid, Ethoxyfen, Ethoxysulfuron, Etobenzanid, Jing Fenoxaprop-methyl, Fentrazamide, Wheatgrass Fluorisopropyl Ester, Wheat Straw Fluoride Isopropyl Ester, Wheat Grass Fluoromethyl Ester, Fluorosulfuron-methyl, Florasulam, Fluorazifop-P-P, Fluazolate, Flucarbazone(-sodium), Flufenacet, Azole Flumesulam, flufenoxalic acid, propargyl flufluramid, Flumipropyn, flumisulfuron, fluorenmeuron, flumetrione, ethyl carboxyfluorfen, flumifenazole, Flupropacil, Flurpyrsulfuron (-methyl, -sodium), fluorenbutyl, fluoxazone, Fluroxypyr(-butoxypropyl, meptyl), fluroxypyr, fluroxypyrimol, furazone, Fluthiacet(-methyl), Fluthiamide, fomesulfazone, Foramsulfuron, Glufosinate-ammonium, Glyphosate (-Isopropylammonium), Halosafen, Haloxyfop, Haloxyfop, Hexazinone, Imazamic Acid, Imazamethapyr, Imazamox, Imazapic, Imazethapyr, Imazaquin, Imazethapyr, Methazosulfuron, Iodosulfuron (-methyl, -sodium), Iodosulfuron, Isopropraline, Isoproturon, Isoprofen, Isoxamid, Isoxachlortole, Isoxaflutole, Clomafen, Lactofen Grass Spirit, Cyclopyr, Rinonglun, MCPA, 2-methyl-4-chloropropionic acid, Mesotrione, Mesotrione, Mesotrione, Mezachlor, Zolone, Pyranuron, Xiugulong , (α-) metolachlor, sulfentrazone, methoxuron, grass kejing, metsulfuron, motilate, chlorguron, naproxen, oxa naphthalene, turfron, nicosulfuron , Dacaojian, Pingcaodan, Amisalazine, Oxadiargyl, Oxadiazone, Oxasulfuron, Oxaziclomefone, Oxyfluorophene, Paraquat, Pelargonic Acid, Pendramansarin, Pendralin, Pentoxazone, Bendicon, Picolinafen , dimethafos, pretilachlor, flurisulfuron-methyl, Profluazol, promethazin, poison aquam, propanil, oxoxalic acid, propachlor, Procarbazone(-sodium), benzamide, profluazol, Flusulfuron-methyl, Pyraflufen(-ethyl), Pyrazogyl, Pyrazolate, Pyrazosulfuron-methyl, Bencloconazole, Pyribernzoxim, Barncloth, Pyridazoate, Pyridatol, Pyriftalid, Pyriminobac(-methyl), Pyrazofen, Quinchlorac, quinclorac, algaequinone, quizalofop-p-ethyl, quizalofofurate, rimsulfuron-methyl, sethoxydim, simazine, sizanet, sulcotrione, sulfentrazone, methazine Sulfosulfuron, Sulfosate, Sulfosulfuron, Phytopyramine, Buthiuron, Tepraloxydim, Terbuthylazine, Trimethazin, Dimethenamid, Thiafluamide, Thiazyronic Acid, Thidiazimin, Thifensulfuron, Grass grass, Zhongcaodan, Trimethylbenzotrione .

Mixtures with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellants, phytonutrients, and active agents which improve the soil structure, are also possible.

The active compounds can be used as such, in their formulations or in the use dosage forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They can be applied in a customary manner, for example by watering, spraying, atomizing, or spreading.

The active compounds according to the invention can be applied both before and after emergence of the plants. The active compounds according to the invention can be incorporated into the soil before sowing.

The amount of active compound used can be varied within relatively wide ranges. The amount used depends essentially on the nature of the effect desired. The amount used is generally from 1 g to 10 kg of active compound per hectare of soil area, preferably from 5 g to 5 kg per hectare.

The preparation and use of the active compounds according to the invention can be seen in the following examples.

Preparation Examples:

Example 1

1.3 g (3 mmol) of 2-[2,4-dichloro-3-[(3-methyl-2-oxo-tetrahydro-1(2H)-pyrimidinyl)-methyl]-benzoyl] - A mixture of cyclohexane-1,3-dione, 1.0 g (7.5 mmol) oxalyl chloride, 2 drops of N,N-dimethylformamide and 30 ml of dichloromethane was heated to reflux for 30 minutes, then concentrated under water pump vacuum . The residue was taken up in 50 ml of tetrahydrofuran and mixed with 0.33 g (3 mmol) of thiophenol. After cooling with ice, 0.50 g (4.5 mmol) of triethylamine was added dropwise. The ice cooling was removed and the mixture was stirred at room temperature for 2 hours and concentrated under water pump vacuum. The residue was taken up in dichloromethane, washed once with 1N hydrochloric acid, water and saturated aqueous sodium chloride, dried over sodium sulfate, and filtered. The filtrate is concentrated under water pump vacuum, the residue is digested with ether and the resulting crystalline product is isolated by suction filtration.

0.91 g (61% yield) of 1-[2,6-dichloro-3-[(6-oxo-2-phenylthio-1-cyclohexen-1-yl)-carbonyl]- Benzyl]-3-methyl-tetrahydro-2(1H)-pyrimidinone, melting point is 140°C.

Following a method analogous to Example 1 and according to the general description of the preparation process of the present invention, compounds of general formula (I) - or compounds of general formula (ID), for example listed in Table 1 below - can also be prepared.

Table 1: Examples of compounds of formula (ID)

The logP values given in Table 1 were determined according to EEC-Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) using a reversed-phase column (C18). Temperature: 43°C.

(a) Mobile phases for determination in the acidic range: 0.1% aqueous phosphoric acid, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile—the corresponding measurement results are marked ^a) in table 1.

(b) Mobile phase for determination in neutral range: 0.01 M phosphate buffered aqueous solution, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile—corresponding measurement results are marked a) in table 1.

Calibration was performed with unbranched alkan-2-ones (having 3-16 carbon atoms) with known logP values (determined by retention time using linear interpolation between two consecutive alkanones) .

The lambda maximum is determined by UV spectroscopy at the maximum chromatographic signal between 200nm and 400nm.

Table 2: Other examples of compounds of formula (I)

Application example:

Example A

pre-emergence test

Solvent: acetone of 5 parts by weight

Emulsifier: 1 part by weight of alkyl aryl polyglycol ether

To prepare a suitable formulation of the active compound, 1 part by weight of the active compound is mixed with the abovementioned amount of solvent, the abovementioned amount of emulsifier is added, and the concentrate is diluted with water to the desired concentration.

Seeds of the test plants were sown in standard soil. After 24 hours, the soil is sprayed with the abovementioned preparation of active compound in such a way that in each case the specific amount of active compound is applied per unit area. The active compound concentration of the spray solutions is selected such that the desired amount of active compound in 1000 liters of water is applied per hectare in each case.

After 3 weeks, the degree of damage to the plants in % damage is assessed by comparison with the untreated control.

Data representation:

0% = no effect (same as untreated control)

100% = complete destruction

In this test, for example the compound of Preparation Example 16 exhibited strong activity against weeds and was well tolerated by certain crops such as maize.

Example B

post-emergence test

Solvent: acetone of 5 parts by weight

Emulsifier: 1 part by weight of alkyl aryl polyglycol ether

To prepare a suitable formulation of the active compound, 1 part by weight of the active compound is mixed with the abovementioned amount of solvent, the abovementioned amount of emulsifier is added, and the concentrate is diluted with water to the desired concentration.

Test plants at a height of 5-15 cm are sprayed with the abovementioned preparation of active compound, so that in each case the desired amount of active compound is applied per unit area. The concentration of the spray solutions is selected such that the desired amount of active compound in 1000 liters of water is applied per hectare in each case.

After 3 weeks, the degree of damage to the plants in % damage is assessed by comparison with the untreated control.

Data representation:

0% = no effect (same as untreated control)

100% = complete destruction

In this test, for example the compounds of Preparation Examples 1, 2, 5, 16, 17, 18, 19 and 20 showed strong activity against weeds and they were well tolerated by certain crops such as maize.

Claims (5)

1. The substituted benzoyl cyclohexenone of formula (I)

in n represents the number 0, A represents a single bond, methylene, ethylene or dimethylene, R ¹ represents hydrogen, ^R represents hydrogen or together with ^R represents methylene, ethylene or trimethylene, R ³ represents fluorine, chlorine, bromine, iodine, methoxy, ethoxy, n-propoxy or isopropoxy, n-butoxy, isobutoxy, sec-butoxy or tert-butoxy, methyl methylsulfonyl, ethylsulfonyl, n-propylsulfonyl or isopropylsulfonyl, R ⁴ represents fluorine, chlorine, bromine, iodine, methoxy, ethoxy, n-propoxy or isopropoxy, n-butoxy, isobutoxy, sec-butoxy or tert-butoxy, methyl methylsulfonyl, ethylsulfonyl, n-propylsulfonyl or isopropylsulfonyl, Y stands for phenyl, Z represents one of the following heterocyclic groups

Q stands for oxygen, ^R represents hydrogen, methyl, ethyl, n-propyl or isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, methoxy, ethoxy, n-propoxy or isopropyl Oxygen, n-butoxy, isobutoxy, sec-butoxy or tert-butoxy, methylthio, ethylthio, n-propylthio or isopropylthio, n-butylthio, isobutylthio , sec-butylthio or tert-butylthio, methylamino, ethylamino, dimethylamino or diethylamino, R ⁶ represents hydrogen, methyl, ethyl, n-propyl or isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl. 2. The compound of claim 1, characterized in that, n represents the number 0, A represents a single bond or represents a methylene group, R ¹ represents hydrogen, ^R represents hydrogen or together with ^R represents methylene, ethylene or trimethylene, R ³ represents fluorine, chlorine, bromine, iodine, methoxy, ethoxy, n-propoxy or isopropoxy, n-butoxy, isobutoxy, sec-butoxy or tert-butoxy, methyl methylsulfonyl, ethylsulfonyl, n-propylsulfonyl or isopropylsulfonyl, R ⁴ represents fluorine, chlorine, bromine, iodine, methoxy, ethoxy, n-propoxy or isopropoxy, methylsulfonyl, ethylsulfonyl, n-propylsulfonyl or isopropylsulfonyl , Y stands for phenyl, Z represents one of the following heterocyclic groups

^R represents hydrogen, methyl, ethyl, n-propyl or isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, methoxy, ethoxy, n-propoxy or isopropyl Oxygen, n-butoxy, isobutoxy, sec-butoxy or tert-butoxy, methylthio, ethylthio, n-propylthio or isopropylthio, n-butylthio, isobutylthio , sec-butylthio or tert-butylthio, methylamino, ethylamino, dimethylamino or diethylamino, R ⁶ represents hydrogen, methyl, ethyl, n-propyl or isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl. 3. Herbicidal compositions, characterized in that they comprise at least one compound according to claim 1 or 2 and customary extenders. 4. Use of at least one compound according to claim 1 or 2 for controlling unwanted vegetation. 5. Method for controlling unwanted plants, characterized in that at least one compound according to claim 1 or 2 is acted on the unwanted plants and/or their habitus.